WO2013146866A1 - Waxy composition and process for producing same - Google Patents

Description

Wax-like composition and method for producing the same

The present invention relates to a waxy composition suitable as a substitute for wax and a method for producing the same.
This application claims priority based on Japanese Patent Application No. 2012-077731 for which it applied to Japan on March 29, 2012, and uses the content here.

In the recent rapid development of industry, industrial products having various chemical structures are used around us. Among them, hydrocarbon compounds using crude oil as a raw material are distributed in various processing methods, forms, or compositions along with the development of the petroleum industry, and are widely used for extremely familiar industrial materials. Among these, compounds called paraffinic hydrocarbons are mainly crude oil separated, refined and fractionated by differences in boiling point, melting point, etc., and are liquid liquid paraffin, solid paraffin wax, or mainly distillation residues thereof. It is classified as petrolatum.
These materials called paraffinic hydrocarbons are used very favorably in the food, chemical industry, pharmaceutical, or cosmetic industries because they are supplied at a very low price because of their huge production scale. It is one of the materials. In various industries, for example, liquid liquid paraffin is used as a base oil for lubricants and cosmetics, and solid paraffin wax is a mold release agent, moldability improver, polish, waterproofing or water repellent, and products. It is used as a base material for imparting a form. Furthermore, petrolatum, which is a pasty hydrocarbon known as petrolatum in Japan, is in the middle of liquid and solid shapes, and is used as a mold release agent or lubricant for ointment bases and industrial products in pharmaceuticals.

Paraffinic hydrocarbons generally contain impurities other than the intended physical properties (for example, boiling point or melting point) because the target fraction is extracted from crude oil containing a large number of compounds by an operation such as distillation. It is known. In particular, among paraffin hydrocarbons, paraffin wax, which is known as a solid component, is a component obtained by subjecting petroleum crude oil to atmospheric distillation and further vacuum distillation or solvent fractionation, and has about 16 to 50 carbon atoms. It consists of the main straight chain hydrocarbon.
For this reason, paraffin wax is also a mixture of many compounds. For example, paraffin 155F, which is known as a paraffin wax, is mixed with about 5 to 10 before and after a hydrocarbon compound having a main melting point of 36 carbon atoms. It is common to include things. For this reason, when using the paraffinic hydrocarbon refined from crude oil for various purposes, some problems occur due to the presence of impurities and contaminants resulting from the origin of the crude oil.

For example, when paraffin wax is used as a mold release agent, as described above, it often contains components having a melting point lower than the target melting point, and these components affect the solidity, resulting in a large influence on the mold release property. Is known to give.
In addition, when paraffin wax is used as a glossing agent, it is known that the crystallinity changes and the optical characteristics are affected by the difference in the component composition.
When paraffin wax is used as a waterproofing or water repellent, it contains a low melting point component that is not intended, resulting in a difference in crystal diameter, resulting in a decrease in water repellency and a decrease in heat resistance. It is also known to reduce.

When paraffin wax is blended in a lipstick, which is a cosmetic material, as a moldability improver or a form-imparting agent, one or more paraffin waxes for cosmetics are generally selected from many. Lipsticks are generally molded by cooling and solidifying the entire mold after pouring it into a mold or the like after mixing and heating a material such as oil or pigment other than paraffin wax by mixing and heating.
It is known that the mixture of these waxes and oils changes the crystal size depending on the cooling rate. This crystal size greatly affects the smoothness of the lipstick surface after solidification, that is, the appearance as an industrial product. Therefore, when selecting the paraffin wax, one that melts at an appropriate temperature during melting and further solidifies at an appropriate temperature during molding is selected.

Furthermore, lipsticks often go through a wide temperature range from low to high during the distribution process. In particular, when transporting at high temperatures during distribution, if the melting point of the wax described above is not appropriate, the wax component melts and loses its shape, or the oil or wax liquefied component contained in the lipstick becomes droplets. A phenomenon called “sweat” that deposits on the surface may occur. From such a background, paraffin wax having a high melting point is preferred for lipstick stability.

On the other hand, lipstick is applied to the lips, which are said to be sensitive to the touch in the human body. For this reason, when the melting point of the wax is too high, the feeling of application is felt very hard, not only the feeling of use is deteriorated, but also the colorability of the lip, which is the original purpose, is lowered. For this reason, paraffin waxes with a relatively low melting point are generally preferred for use feeling of lipstick.

For the reasons described above, paraffin waxes are selected with low melting point properties that do not impair the feeling of use and high melting point components with excellent stability, when selecting paraffin waxes. However, there are some low melting point or high melting point components that are more than intended. This can greatly reduce the stability and usability of lipsticks sometimes formulated.

When paraffin wax is used for hair wax, especially for emulsifying hair conditioners, the hydrophilic / lipophilic balance of the surfactant necessary for emulsification (general It is known that the stability of cosmetics is greatly affected.

On the other hand, industrial materials using these hydrocarbon materials are demanded as a recent global trend that the environmental load in the production process is small. For example, industrial materials using these hydrocarbon materials have less carbon dioxide emissions and less environmental impact when the raw material is derived from plants or microbial fermentation than from fossil fuels. It is believed that. In addition, when the industrial materials are discharged after use, if the raw materials of the industrial materials are derived from plants or from microbial fermentation, it is considered that they are easily decomposed by microorganisms in rivers and soils and have a low environmental load. Yes. Furthermore, carbon contained in industrial resources originating from constituents of living organisms such as plants and microorganisms is different from carbon contained in fossil fuels, and the living organisms absorb from the atmosphere by photosynthesis during the growth process. Derived from carbon dioxide. Therefore, even if these industrial resources are used, it is considered that there is no effect on the increase or decrease in the total amount of carbon dioxide in the atmosphere (hereinafter, sometimes referred to as the concept of carbon neutral). From the above, it is considered that when the raw material is derived from animals or plants or microbial fermentation, the environmental load is less when industrial materials are discharged into the environment after use than those derived from crude oil.

Thus, several methods for producing a hydrocarbon material with less environmental load are disclosed.
For example, Patent Document 1 discloses a method for producing a hydrocarbon-based oil by ketonization, hydrodeoxygenation, and isomerization of a raw material oil derived from a living body such as vegetable oil. Patent Document 2 discloses a method for obtaining a hydrocarbon mixture by reductive dehydroxymethylation of vegetable fatty alcohol.

Special table 2009-518530 gazette Special table 2010-531809 gazette

However, the biological hydrocarbon compositions produced in Patent Documents 1 and 2 are all liquid compositions, and it is very difficult to produce a wax-like composition that can be used as a wax substitute. there were.

The present invention has been made in view of the above circumstances, and compared with existing hydrocarbon compositions, the content of contaminants other than the intended components is reduced, and the moldability, stability, and mold release are reduced. Provided are a hydrocarbon composition having excellent properties, water repellency, waterproofness, and antiblocking properties, and having reduced environmental load, and a method for producing the same.

Unless otherwise specified, in this specification, “fatty acid” refers to a hydrocarbon compound in which any one or more hydrogen atoms are substituted with a carboxyl group. The “saturated fatty acid” refers to a fatty acid in which all carbon-carbon bonds on the main hydrocarbon chain are single bonds. “Unsaturated fatty acid” refers to a fatty acid having at least one double bond or triple bond in the carbon-carbon bond on the main hydrocarbon chain. “Straight chain fatty acid” refers to a fatty acid having no carbon-carbon bond branched into a main hydrocarbon chain. “Branched fatty acid” refers to a fatty acid having a carbon-carbon bond branched to a main hydrocarbon chain among fatty acids, and more specifically, “isostearic acid”, “branched monomer acid”, “dimer acid” or “ "Trimer acid".

As a result of intensive studies to solve the above problems, the present inventors have used a fatty acid composition having a specific fatty acid composition as a raw material, and performed a decarboxylative dimerization reaction on the fatty acid composition. Later, the hydrodeoxygenation reaction was performed on the resulting aliphatic ketone to find that a wax-like hydrocarbon composition was obtained, and the present invention was completed.

That is, the method for producing the wax-like composition, the wax-like composition, and the method for using the wax-like composition of the present invention have the following aspects [1] to [24], for example.
[1] Fatty acid composition is
(1) The content of linear fatty acid is 30% by mass or more and 100% by mass or less, or (2) the content of linear fatty acid is 25% by mass or more and less than 30% by mass, and 2 or 3 carvone Does not contain liquid branched chain fatty acids at 25 ° C. with acid or the content is below the detection limit,
Production of a wax-like composition, wherein a decarboxylative dimerization reaction is performed on a fatty acid composition, and then a hydrodeoxygenation reaction is performed on the resulting composition containing an aliphatic ketone. Method.
[2] The branched fatty acid having 2 or 3 carboxylic acids which is liquid at 25 ° C. has a branched chain fatty acid having 36 carbon atoms having 2 carboxylic acids and a branched chain having 54 carbon atoms having 3 carboxylic acids. The method for producing a waxy composition according to the above [1], which is one or more selected from the group consisting of chain fatty acids.
[3] The wax form according to [1] or [2], wherein the content of the linear fatty acid having two carboxylic acids is ½ or less of the content of the linear fatty acid having one carboxylic acid. A method for producing the composition.
[4] The waxy composition according to any one of [1] to [3], wherein the linear fatty acid having two carboxylic acids is a linear fatty acid having 4 to 10 carbon atoms having two carboxylic acids. Manufacturing method.
[5] The method for producing a waxy composition according to any one of [1] to [4], wherein the linear fatty acid having one carboxylic acid in the fatty acid composition has 10 to 22 carbon atoms.
[6] The decarboxylation dimerization reaction is performed in the presence of one or more selected from the group consisting of Group II, Group VII to XII metal atoms, and any one of [1] to [5] above A method for producing a waxy composition.
[7] The decarboxylation dimerization reaction is performed in the presence of one or more metals selected from the group consisting of Mg, Ca, Mn, Fe, Co, Ni, Cu, and Zn. A method for producing a wax-like composition according to any one of [6] to [6].
[8] The method for producing a waxy composition according to [7], wherein the metal is an oxide or a hydroxide.
[9] The fatty acid composition is
(1) The content of linear fatty acid is 30% by mass or more and 100% by mass or less, or (2) the content of linear fatty acid is 25% by mass or more and less than 30% by mass, and 2 or 3 carvone Does not contain liquid branched chain fatty acids at 25 ° C. with acid or the content is below the detection limit,
Including an aliphatic ketone obtained after decarboxylation of a metal soap synthesized by a fatty acid composition and one or more selected from the group consisting of Group II and Group VII to XII metal atoms A method for producing a wax-like composition, wherein a hydrodeoxygenation reaction is performed on the composition.
[10] The method for producing a waxy composition according to [9], wherein the metal soap is composed of an alkaline earth metal bonded to two linear fatty acid residues.
A method for producing a waxy composition.
[11] The method for producing a waxy composition according to [9] or [10], wherein the metal soap is magnesium stearate.
[12] The hydrodeoxygenation reaction is a reaction in which a ketone group is reduced to a methylene group, and is performed in the presence of hydrazine or zinc amalgam, and the waxy form according to any one of [1] to [11] A method for producing the composition.
[13] The hydrodeoxygenation reaction is
A reduction reaction of the ketone for reducing the aliphatic ketone and synthesizing the aliphatic alcohol;
Intramolecular dehydration reaction in which the obtained aliphatic alcohol is dehydrated intramolecularly to form an unsaturated bond;
A reduction reaction of the unsaturated bond to obtain a saturated hydrocarbon by reducing the hydrocarbon in which the unsaturated bond is formed by the intramolecular dehydration reaction;
A process for producing a waxy composition according to any one of the above [1] to [11].
[14] At least one of the reduction reaction of the ketone and the reduction reaction of the unsaturated bond is selected from the group consisting of Pt, Pd, Ni, Cu, Cr, Ru, Rh, Li, Al, B, and Zn. The method for producing a waxy composition according to [13], which is performed in the presence of one or more.
[15] The method for producing a waxy composition according to [13], wherein the intramolecular dehydration reaction is performed in the presence of a Bronsted acid and / or a Bronsted base.
[16] Any of [1] to [15] above, wherein the ratio of ¹⁴ C isotope to ¹² C isotope in the fatty acid composition is in the range of 6 × 10 ⁻¹³ to 1.2 × 10 ⁻¹² . A method for producing a waxy composition.
[17] The wax-like composition production method according to any one of [1] to [16], wherein the ratio of ¹⁴ C isotope to ¹² C isotope is 6 × 10 ⁻¹³ to 1.2 × 10 A waxy composition, characterized in that it is in the range of ^-12 .
[18] The waxy composition according to [17], which is used as a substitute for paraffin wax.
[19] The wax-like composition according to [17], which is used as a mold release improver.
[20] The wax-like composition according to [17], which is used as a moldability improver.
[21] The wax-like composition according to [17], which is used as a polish.
[22] The wax-like composition according to [17], which is used as a waterproof or water-repellent imparting agent.
[23] The wax-like composition of the above [17] used for cosmetics.
[24] The fatty acid composition is
(1) The content of linear fatty acid is 30% by mass or more and 100% by mass or less, or (2) the content of linear fatty acid is 25% by mass or more and less than 30% by mass, and 2 or 3 carvone Does not contain liquid branched chain fatty acids at 25 ° C. with acid or the content is below the detection limit,
A waxy composition obtained by subjecting a fatty acid composition to a decarboxylative dimerization reaction and then subjecting the resulting composition containing an aliphatic ketone to a hydrodeoxygenation reaction is A method for using a wax-like composition, characterized by being used as a substitute for a wax.

The present invention has the following aspects.
[1] Fatty acid composition is
(1) The content of linear fatty acids is 30% by mass or more and 100% by mass or less with respect to the total mass of total fatty acids, or (2) the content of linear fatty acids is 25% by mass with respect to the total mass of total fatty acids. % Is less than 30% by mass and does not contain a branched chain fatty acid that is liquid at 25 ° C. having 2 or 3 carboxylic acids, or the content is below the detection limit,
A method for producing a waxy composition, comprising performing a decarboxylation dimerization reaction on a fatty acid composition, and then performing a hydrodeoxygenation reaction on the resulting composition containing an aliphatic ketone,
[2] The branched fatty acid having 2 or 3 carboxylic acids which is liquid at 25 ° C. has a branched chain fatty acid having 36 carbon atoms having 2 carboxylic acids and a branched chain having 54 carbon atoms having 3 carboxylic acids. The method for producing a waxy composition according to [1], which is at least one fatty acid selected from the group consisting of chain fatty acids,
[3] The linear fatty acid contains at least one linear fatty acid selected from the group consisting of a linear fatty acid having one carboxylic acid and a linear fatty acid having two carboxylic acids,
The content of the linear fatty acid having the two carboxylic acids with respect to the total mass of the total fatty acids is ½ or less of the content with respect to the total mass of the linear fatty acids, [1] or [2 ], A method for producing a waxy composition according to
[4] The linear fatty acid having two carboxylic acids is a linear fatty acid having 4 to 10 carbon atoms having two carboxylic acids, according to any one of [1] to [3]. A method for producing a waxy composition,
[5] The waxy form according to any one of [1] to [3], wherein the linear fatty acid having one carboxylic acid in the fatty acid composition is a linear fatty acid having 10 to 22 carbon atoms. Production method of the composition,
[6] The decarboxylation dimerization reaction is carried out in the presence of at least one metal atom selected from the group consisting of Group II and Group VII to XII metal atoms, [1] to [5] A method for producing the wax-like composition according to any one of the above,
[7] The decarboxylation dimerization reaction is performed in the presence of at least one metal selected from the group consisting of Mg, Ca, Mn, Fe, Co, Ni, Cu, and Zn. [6] The method for producing a waxy composition according to any one of
[8] The method for producing a wax-like composition according to [7], wherein the metal is an oxide or a hydroxide.
[9] Fatty acid composition is
(1) The content of linear fatty acids is 30% by mass or more and 100% by mass or less with respect to the total mass of total fatty acids, or (2) the content of linear fatty acids is 25% by mass with respect to the total mass of total fatty acids. % Is less than 30% by mass and does not contain a branched chain fatty acid that is liquid at 25 ° C. having 2 or 3 carboxylic acids, or the content is below the detection limit,
Fat obtained by performing decarboxylation on a metal soap synthesized with a fatty acid composition and at least one metal atom selected from the group consisting of Group II and Group VII to XII metal atoms Performing a hydrodeoxygenation reaction on a composition containing an aromatic ketone, a method for producing a wax-like composition,
[10] The method for producing a wax-like composition according to [9], wherein the metal soap is composed of an alkaline earth metal bonded to two linear fatty acid residues,
[11] The wax-like material according to [9], wherein the metal soap is a metal soap containing at least one metal selected from the group consisting of Mg, Ca, Mn, Fe, Co, Ni, Cu, and Zn. Production method of the composition,
[12] The hydrodeoxygenation reaction is a reaction in which a ketone group is reduced to a methylene group, and is carried out in the presence of hydrazine or zinc amalgam, according to any one of [1] to [11] A method for producing a waxy composition of
[13] The hydrodeoxygenation reaction is
A reduction reaction of the ketone for reducing the aliphatic ketone and synthesizing the aliphatic alcohol;
Intramolecular dehydration reaction in which the obtained aliphatic alcohol is dehydrated intramolecularly to form an unsaturated bond;
A reduction reaction of the unsaturated bond to obtain a saturated hydrocarbon by reducing the hydrocarbon in which the unsaturated bond is formed by the intramolecular dehydration reaction;
The method for producing a wax-like composition according to any one of [1] to [11],
[14] At least one of the reduction reaction of the ketone and the reduction reaction of the unsaturated bond is selected from the group consisting of Pt, Pd, Ni, Cu, Cr, Ru, Rh, Li, Al, B, and Zn. The method for producing a waxy composition according to [13], which is performed in the presence of at least one metal,
[15] The method for producing a wax-like composition according to [13], wherein the intramolecular dehydration reaction is performed in the presence of at least one of a Bronsted acid and a Bronsted base.
[16] The ratio of the molar abundance ratio of ¹⁴ C isotope to the molar abundance ratio of ¹² C isotope in the fatty acid composition is in the range of 6 × 10 ⁻¹³ to 1.2 × 10 ^−12. To [15], a method for producing the wax-like composition according to any one of
[17] The method for producing a wax-like composition according to any one of [1] to [16], wherein the ratio of the molar abundance ratio of ¹⁴ C isotope to the molar abundance ratio of ¹² C isotope is: A waxy composition in the range of 6 × 10 ⁻¹³ to 1.2 × 10 ⁻¹² ,
[18] The waxy composition according to [17], which is used as a substitute for paraffin wax,
[19] The waxy composition according to [17], which is used as a mold release improver,
[20] The waxy composition according to [17], which is used as a moldability improver,
[21] The wax-like composition according to [17], which is used as a polish.
[22] The wax-like composition according to [17], which is used as a waterproof or water-repellent imparting agent,
[23] The waxy composition according to [17], which is used in cosmetics,
[24] The fatty acid composition is
(1) The content of linear fatty acids is 30% by mass to 100% by mass with respect to the total mass of total fatty acids, or (2) the content of linear fatty acids is 25% with respect to the total mass of total fatty acids. % Is less than 30% by mass and does not contain a branched chain fatty acid that is liquid at 25 ° C. having 2 or 3 carboxylic acids, or the content is below the detection limit,
A waxy composition obtained by subjecting a fatty acid composition to a decarboxylative dimerization reaction and then subjecting the resulting composition containing an aliphatic ketone to a hydrodeoxygenation reaction is A method of using a waxy composition comprising using as a substitute for a wax;
[25] Use of the waxy composition according to [17] as a substitute for paraffin wax,
[26] Use of the wax-like composition as described in [17] as a releasability improver,
[27] Use of the waxy composition according to [17] as a moldability improver,
[28] Use of the waxy composition according to [17] as a polish,
[29] Use of the wax-like composition as described in [17] as a waterproof or water-repellent imparting agent, and use of the wax-like composition as described in [30] and [17] as cosmetics.

The wax-like hydrocarbon composition suitable for various industrial materials can be obtained from the fatty acid composition having a specific fatty acid composition by the method for producing a wax-like composition of the present invention. The wax-like composition obtained by the method can significantly reduce the content of impurities and contaminants compared to a wax-like hydrocarbon composition refined from crude oil, moldability, stability, Excellent releasability, water repellency, waterproofness and anti-blocking property. Furthermore, a waxy hydrocarbon composition with reduced environmental burden can be obtained by using a biological fatty acid composition as a raw material. For this reason, the wax-like composition obtained by the said method is suitable mainly as a substitute of paraffin wax, and can be widely used for various industrial materials.

It is the figure which showed typically the evaluation method of mold release property. It is the figure which showed typically the evaluation method of mold release property. It is the figure which showed typically the evaluation method of mold release property.

<Method for producing wax-like composition>
The method for producing a wax-like composition of the present invention is such that a fatty acid composition comprising a specific fatty acid composition is subjected to decarboxylation dimerization reaction, and then the resulting composition containing an aliphatic ketone is hydrogenated. It is characterized by performing a deoxygenation reaction. By using a fatty acid composition having a specific fatty acid composition as a raw material, a waxy composition can be obtained.

In the present invention and the specification of the present application, a straight-chain fatty acid is a straight-chain hydrocarbon (compound composed of carbon and hydrogen), which is a compound having one or two carboxylic acids. That is, a straight-chain fatty acid having one carboxylic acid is a compound in which one of the hydrogen atoms bonded to the carbon atom at one end of the straight-chain hydrocarbon is substituted with a carboxyl group. . In the linear fatty acid having two carboxylic acids, one hydrogen atom bonded to the carbon atoms at both ends of the linear hydrocarbon is substituted with a carboxyl group.

In the present invention and the present specification, a branched chain fatty acid is a hydrocarbon having a branched chain and having one or more carboxylic acids. That is, it is a compound in which one or more hydrogen atoms of a branched hydrocarbon are substituted with a carboxyl group.

[Fatty acid composition]
The fatty acid composition used as a raw material consists of a fatty acid composition having any of the following characteristics (1) or (2).
(1) The content of linear fatty acids is 30% by mass or more and 100% by mass or less with respect to the total mass of total fatty acids.
(2) The content of linear fatty acids is 25% by mass or more and less than 30% by mass with respect to the total mass of total fatty acids, and does not contain liquid branched chain fatty acids at 25 ° C. having 2 or 3 carboxylic acids. Alternatively, the content is below the detection limit.
Each characteristic will be described below.

The fatty acid composition has a linear fatty acid content of 25% by mass or more based on the total mass of total fatty acids. The content of the straight chain fatty acid in the fatty acid composition may be 25% by mass or more with respect to the total mass of the total fatty acids, may be 100% by mass, and is preferably 25 to 60% by mass. 25 to 50% by mass is more preferable. When the content of the linear fatty acid in the fatty acid composition is 25% by mass or more with respect to the total mass of the total fatty acids, the obtained hydrocarbon composition can be made into a wax form. When the content of linear fatty acid is low, the produced hydrocarbon composition tends to be pasty or liquid, and it is difficult to produce a wax-like composition.

The linear fatty acid contained in the fatty acid composition may be only one type or two or more types. Moreover, it may be liquid at 25 ° C., it may be solid, and it may have one carboxylic acid or two. Furthermore, the linear fatty acid contained in the fatty acid composition may be a saturated fatty acid only, an unsaturated fatty acid only, or both a saturated fatty acid and an unsaturated fatty acid. In the method for producing a wax-like composition of the present invention, as described later, the unsaturated bond in the reaction composition is finally converted into a saturated bond by a reduction reaction, so that the saturated fatty acid in the fatty acid composition as a raw material and Regardless of the content ratio of the unsaturated fatty acid, a wax-like composition containing a saturated hydrocarbon as a main component can be obtained.

The linear fatty acid contained in the fatty acid composition is preferably a linear fatty acid having one carboxylic acid having 8 to 22 carbon atoms or a linear fatty acid having two carboxylic acids having 4 to 10 carbon atoms. Specifically, as the linear fatty acid having one carboxylic acid, caprylic acid (octanoic acid), capric acid (decanoic acid), lauric acid (dodecanoic acid), myristic acid (tetradecanoic acid), palmitic acid (hexadecane) Acid), stearic acid (octadecanoic acid), oleic acid (cis-9-octadecenoic acid), linoleic acid (octadecadienoic acid), linolenic acid (octadecanetrienoic acid), arachidic acid (eicosanoic acid), erucic acid (docosenoic acid) ) Or behenic acid (docosanoic acid) and the like, and capric acid (decanoic acid), lauric acid (dodecanoic acid), myristic acid (tetradecanoic acid), palmitic acid (hexadecanoic acid), stearic acid (octadecanoic acid), olein Acid (cis-9-octadecenoic acid), linoleic acid (octadecadienoic acid), linolene (Octa decanted Lien acid), arachidic acid (eicosanoic acid), erucic acid (docosenoic acid) or behenic acid (docosanoic acid) are preferred. Examples of the linear fatty acid having two carboxylic acids include sebacic acid having 10 carbon atoms. In the present invention, the fatty acid composition contains both a linear fatty acid having one carboxylic acid having 10 to 22 carbon atoms and a linear fatty acid having two carboxylic acids having 4 to 10 carbon atoms. Preferably, it contains a linear fatty acid having one carboxylic acid having 10 to 22 carbon atoms and sebacic acid.

In the present invention, the content of the linear fatty acid having one carboxylic acid contained in the fatty acid composition is preferably 10% by mass or more based on the total mass of the total fatty acids, and is 10 to 60% by mass. More preferably, it is 16 to 50% by mass, further preferably 30 to 50% by mass.

In addition, the fatty acid composition preferably contains a linear fatty acid having two carboxylic acids, and more preferably contains sebacic acid. When sebacic acid is contained, the content thereof is preferably 1 to 15% by mass, and more preferably 1 to 10% by mass with respect to the total mass of the total fatty acids. When the fatty acid composition contains a linear fatty acid having two carboxylic acids, the total mass of the total fatty acids of the linear fatty acids having two carboxylic acids from the viewpoint of the reaction efficiency of the aliphatic ketone synthesis. The content with respect to the total fatty acid content of all the fatty acids in the fatty acid composition is preferably ½ or less, more preferably 2/5 or less, more preferably 3 / More preferably, it is 25 or less, and may be 0.

However, when the content of the linear fatty acid in the fatty acid composition is 25% by mass or more and less than 30% by mass with respect to the total mass of the total fatty acids, the fatty acid composition contains 2 or 3 carboxylic acids. Does not contain liquid branched-chain fatty acids (hereinafter sometimes referred to as “liquid branched-chain dimer acid or trimer acid”) at 25 ° C., or the content thereof is extremely small below the detection limit. It takes a thing. When the content is less than 30% by mass with respect to the total mass of the total fatty acids of the linear fatty acids, and the liquid branched dimer acid or trimer acid is also contained, the produced hydrocarbon composition is pasty. It tends to become liquid, and it is difficult to produce a waxy composition.

The “branched fatty acid that is liquid at 25 ° C.” means that the branched fatty acid or linear fatty acid is liquid when the temperature is 25 ° C. That is, when the branched-chain fatty acid or the straight-chain fatty acid is at a temperature other than 25 ° C., the liquid state changes depending on the temperature. The branched chain fatty acid or straight chain fatty acid in such a changed state is also included in the “branched chain fatty acid that is liquid at 25 ° C.”.
In other words, even if the state of the branched-chain fatty acid or straight-chain fatty acid at a certain temperature is not liquid, the liquid branched-chain fatty acid or straight-chain fatty acid is 25 ° C. Included in "fatty acid".

Examples of the liquid branched dimer acid or trimer acid include branched chain fatty acids having 2 or 3 carboxylic acids having 10 to 54 carbon atoms. Specific examples include compounds obtained by intermolecular polymerization reaction of two or three molecules of unsaturated fatty acid having one carboxylic acid having 6 to 20 carbon atoms. The liquid branched dimer acid or trimer acid may be any fatty acid that is a liquid fatty acid at 25 ° C. having at least one branched chain structure, and a molecule in which linear unsaturated fatty acids form a branched chain structure. The compound obtained by carrying out interpolymerization reaction may be sufficient, and the compound obtained by carrying out intermolecular polymerization reaction of branched chain unsaturated fatty acids may be sufficient. Specifically, a dibasic acid having 36 carbon atoms (branched fatty acid having two carboxylic acids) obtained by an intermolecular polymerization reaction of two molecules of oleic acid, linoleic acid, or linolenic acid, or three molecules Examples thereof include tribasic acids having 54 carbon atoms (branched fatty acids having three carboxylic acids) obtained by the intermolecular polymerization reaction of oleic acid, linoleic acid, or linolenic acid.

The fatty acid composition may contain other fatty acids as long as the fatty acid composition (1) or (2) is satisfied. For example, the fatty acid composition may contain one type or two or more types of branched chain fatty acids.

The number of carbon atoms and the number of carboxylic acids in the branched chain fatty acid contained in the fatty acid composition is not particularly limited. For example, the branched chain chain has 5 to 54 carbon atoms and 1 to 3 carboxylic acids. Fatty acids are mentioned. Further, the branched chain fatty acid contained in the fatty acid composition may be a saturated fatty acid only, an unsaturated fatty acid only, or both a saturated fatty acid and an unsaturated fatty acid.

The fatty acid composition preferably contains a branched fatty acid that is liquid at 25 ° C. (hereinafter sometimes referred to as “liquid branched monomeric acid”) having one carboxylic acid. When the fatty acid composition contains a branched chain fatty acid, the crystallinity of the obtained wax-like composition can be reduced, and flexibility and viscosity can be increased. The content of the monomeric acid in the liquid branched chain is preferably 35 to 75% by mass and more preferably 35 to 60% by mass with respect to the total mass of the total fatty acids.

Examples of the liquid branched monomeric acid include branched chain fatty acids having one carboxylic acid having 5 to 20 carbon atoms. Specifically, isovaleric acid (isopentanoic acid), isocaproic acid (isohexanoic acid), isoenanthic acid (isoheptanoic acid), isocaprilic acid (isooctanoic acid), isoperargonic acid (isononanoic acid), isocapriic acid (isodecanoic acid), iso Undecanoic acid, isolauric acid (isododecanoic acid), isotridecylic acid (isotridecanoic acid), isomyristic acid (isotetradecanoic acid), isopentadecyl acid (isopentadecanoic acid), isopalmitic acid (isohexadecanoic acid), isomalagic acid (isoheptadecanoic acid) ), Isostearic acid (isooctadecanoic acid, 2-heptylundecanoic acid), isononadecylic acid (isonononadecanoic acid), and at least one branched chain fatty acid selected from the group consisting of isoarachidic acid (isoicosanoic acid), Sosutearin acid is more preferable. The fatty acid composition may contain only one type of liquid branched monomeric acid, or may contain two or more types of liquid branched monomeric acid.

Each fatty acid in the fatty acid composition may be refined from crude oil, synthesized from hydrogen gas and carbon dioxide gas, or derived from a living organism (derived from animals or plants or yeast fermentation) May be). A synthetic product or a biological one is preferable because contamination with unexpected impurities or the like can be suppressed, and a biological one is more preferable from the viewpoint of reducing environmental burden. Fatty acids derived from crude oil do not contain ¹⁴ C isotopes, but synthetic products using gas as raw materials and biologically derived fatty acids contain ¹⁴ C isotopes, and the molar abundance ratio of ¹² C isotopes The ratio of the molar abundance ratio of ¹⁴ C isotope with respect to is in the range of 6 × 10 ⁻¹³ to 1.2 × 10 ⁻¹² .

The production method and origin of the above-mentioned biological fatty acid are not limited as long as it is derived from plant, animal or yeast fermentation. The plant fatty acid may be any one obtained by treating plant fat, vegetable oil, plant wax, or the like by treatment such as hydrolysis, acidic transesterification, thermal decomposition, or enzymatic degradation. Examples of the plant include soybean, palm, palm kernel, rapeseed, sunflower, cotton seed, peanut, palm, corn, olive, sesame, flaxseed, castor, pine, macadamia nut, and meadowweed. The animal fatty acid may be any animal fatty acid, animal oil, or animal wax that is obtained by hydrolysis, acidic transesterification, thermal decomposition, enzymatic decomposition, or the like. Examples of animals include cows, pigs, sheep, goats, fish, and whales. In addition, when a fatty chain is obtained from a microbial fermented product, the microorganism to be used is not particularly limited as long as a fatty acid can be obtained by extraction of a culture medium and microbial cells.

The ¹⁴ C content of the sample can be measured in a liquid scintillation spectrometer by counting ¹⁴ C isotopes that decompose in the counter (Libby counter method) or by accelerator mass spectrometry. Accelerator mass spectrometry (abbreviation: AMS) uses nuclear physics analysis to analyze ¹⁴ C isotopes in very small samples (milligram range) in the ppt to ppq range (10 ⁻¹² to 10 ⁻¹⁶ ). It can be detected.

In preparing the fatty acid composition, the fatty acid may be added as it is, or may be added in the state of various salts such as an alkali metal salt.

[Decarboxylative dimerization reaction]
In the method for producing a waxy composition of the present invention, first, a fatty acid in the fatty acid composition is subjected to a decarboxylation dimerization reaction to obtain an aliphatic ketone. In the present invention, the method of decarboxylating and dimerizing each carboxylic acid of two molecules of fatty acid is not particularly limited, and can be performed using a known chemical reaction.

For example, after synthesizing a metal soap having a carbon number of [2n] from two fatty acid molecules having a carbon number of [n], the fatty acid having a carbon number of [2n-1] is obtained by decarboxylation by pyrolysis. A ketone is obtained.
The synthesis of the metal soap can be performed, for example, by a saponification reaction using an alkaline earth metal or a metal. As the metal, for example, at least one metal atom selected from the group consisting of Group II and Group VII to XII metal atoms can be used, and Mg, Ca, Mn, Fe, Co, Ni, Cu, And at least one metal selected from the group consisting of Zn. The metal is more preferably used as an oxide or a hydroxide. In the present invention, it is particularly preferable to use magnesium oxide, magnesium hydroxide, calcium oxide, calcium hydroxide, zinc oxide, zinc hydroxide, or the like.
The thermal decomposition temperature and reaction time of the metal soap are not particularly limited as long as the temperature and time are sufficient for the decarboxylation reaction to occur. For example, the metal soap can be decarboxylated by heating at 140 to 400 ° C., preferably 160 to 340 ° C. for 5 to 30 hours, preferably 10 to 24 hours.

In the decarboxylation dimerization reaction, the fatty acid residue constituting the fatty acid composition or metal soap is (1) the content of linear fatty acid is 30% by mass or more and 100% by mass or less with respect to the total mass of total fatty acids. Or (2) a branched chain which is liquid at 25 ° C. and has 2 or 3 carboxylic acids, wherein the content of linear fatty acids is 25% by mass or more and less than 30% by mass with respect to the total mass of total fatty acids The fatty acid composition ratio is not limited as long as it does not contain a fatty acid or has a fatty acid composition whose content is below the detection limit. Furthermore, the metal used in the decarboxylation dimerization reaction only needs to satisfy the conditions of the metal atom, and the amount of the metal oxide or metal hydroxide used in the decarboxylation dimerization reaction is a fatty acid composition. The combination and the ratio thereof are not limited as long as the amount can neutralize the carboxylic acid of the product. Furthermore, a solvent or a catalyst can be used as long as it does not inhibit decarboxylation of the fatty acid composition.

In the method for producing a wax-like composition of the present invention, the step of synthesizing metal soap from the fatty acid composition can be omitted. That is, instead of performing the decarboxylation dimerization reaction using the fatty acid composition as a raw material, a metal soap is used as a raw material, and the metal soap is decarboxylated by thermal decomposition to be used for a subsequent hydrodeoxygenation reaction. Aliphatic ketones may be obtained. As the metal soap used as a raw material, one having a fatty acid residue composition similar to that obtained by saponifying the fatty acid composition is used. Specific examples include metal soaps synthesized from the fatty acid composition and at least one metal selected from the group consisting of Group II and Group VII to XII metal atoms.
The method for producing a wax-like composition according to another aspect of the present invention is preferably a metal soap made of an alkaline earth metal bonded to two linear fatty acid residues as the metal soap.
In another aspect of the present invention, a method for producing a wax-like composition uses a metal soap containing at least one metal selected from the group consisting of Mg, Ca, Mn, Fe, Co, Ni, Cu, and Zn. A metal soap containing at least one metal selected from the group consisting of Mg, Ca, and Zn is preferable. For example, instead of using a composition consisting only of stearic acid as the fatty acid composition and performing a saponification reaction using magnesium and thermally decomposing the resulting metal soap (magnesium stearate), magnesium stearate is directly used as a raw material. This may be pyrolyzed.
A commercial item can also be used for the said metal soap, and what was chemically synthesized can also be used for it.

Moreover, the manufacturing method of the metal soap is not particularly limited. For example, by a method (direct method) in which a metal soap, a metal hydroxide, or other carbonate is added to a reaction vessel and heated directly to atmospheric pressure or under pressure to obtain a metal soap (direct method), or a fatty acid It is prepared by conventional methods such as the method of reacting with monovalent alkaline earth metals such as Na and K in water to synthesize fatty acid soap and then exchanging metal with divalent metal chloride (metathesis method). Can be used.

[Hydrodeoxygenation reaction]
By performing hydrodeoxygenation reaction on the composition containing the aliphatic ketone obtained by the decarboxylative dimerization reaction, a wax-like composition containing saturated hydrocarbon as a main component is obtained.
The hydrodeoxygenation reaction is not particularly limited as long as it is a reaction that can convert the ketone group of the aliphatic ketone to a methylene group, and can be performed by appropriately combining known chemical reactions.

The hydrodeoxygenation reaction may be a reduction reaction in which a ketone group in an aliphatic ketone is directly reduced to a methylene group, such as Wolf Kishner reduction or Clementen reduction. The Wolf Kishner reduction and the Clementen reduction can be performed by a conventional method. For example, in Wolf Kishner reduction, hydrazine and a base (for example, sodium hydroxide) are added to an aliphatic ketone dissolved in a solvent such as dimethyl sulfoxide or diethylene glycol, and reacted at room temperature to 200 ° C. In the Clementen reduction, zinc amalgam is added to and reacted with an aliphatic ketone dissolved in a strongly acidic solvent such as hydrochloric acid. In addition, the aliphatic ketone can be directly reduced by catalytic hydrogenation using a palladium catalyst in the presence of hydrogen gas.

The hydrodeoxygenation reaction includes a reduction reaction of a ketone that reduces the aliphatic ketone and synthesizes an aliphatic alcohol, and an intramolecular dehydration reaction that forms an unsaturated bond by intramolecular dehydration of the obtained aliphatic alcohol. And a reduction reaction of the unsaturated bond in which unsaturated hydrocarbons are formed by the intramolecular dehydration reaction to obtain saturated hydrocarbons. The reaction at each stage can be performed by a conventionally known chemical reaction. These three-stage reactions can all be carried out continuously in one reaction system, or only two of these reactions can be carried out simultaneously in one reaction system. It can also be performed sequentially in the reaction system.

For example, a reduction reaction of a ketone that synthesizes an aliphatic alcohol (that is, a reaction that reduces a carbon-oxygen double bond of a carbonyl group to convert it to a hydroxyl group), or a reduction reaction of an unsaturated bond to a saturated bond (that is, a fatty acid) The reaction of reducing the carbon-carbon double bond therein to convert it to a carbon-carbon single bond) can be performed by a known reduction reaction. Further, both the reduction reactions may be carried out by a reduction reaction using the same catalyst, or may be carried out by a reduction reaction using different catalysts.
In the present invention, at least one metal selected from the group consisting of Pt, Pd, Ni, Cu, Cr, Ru, Rh, Li, Al, B, and Zn is used as a catalyst in an environment in which hydrogen gas is introduced. It is preferable to carry out the reduction reaction. In addition, Birch reduction using Li as a catalyst can be performed in the presence of liquid ammonia.

Further, the intramolecular dehydration reaction is not particularly limited as long as it is a reaction for dehydrating an aliphatic alcohol in the molecule. For example, a dehydration reaction can be performed by using at least one of a Bronsted acid and a Bronsted base as a catalyst and heating in the presence of these. The reaction temperature and time can be appropriately adjusted in consideration of the type of catalyst used, the amount of aliphatic alcohol used in the reaction, and the like. For example, the reaction can be performed at 80 to 250 ° C. for 1 to 10 hours.

Examples of Bronsted acid include acid catalysts such as activated clay, zeolite, or alumina. Examples of the Bronsted base include aluminum hydroxide and sodium hydroxide.

As long as the hydrodeoxygenation reaction proceeds at each stage, the type and amount of the catalyst and solvent are not particularly limited. For example, in the step of obtaining an alcohol from an aliphatic ketone and the step of obtaining a saturated hydrocarbon from an unsaturated hydrocarbon, 0.01 to 50 wt% of the catalyst can be used with respect to the aliphatic ketone. The catalyst may be a single metal, a metal oxide, or a state where the metal oxide is supported on another inorganic compound. As the metal element, at least one metal element selected from the group consisting of Pt, Pd, Ni, Cu, Cr, Ru, Rh, Li, Al, B, and Zn is preferable, and Pd, Ni, Cu, Cr, And at least one metal element selected from the group consisting of Ru and Ru. Further, in the same step, a solvent may be appropriately used as long as it does not inhibit the reaction. Solvents include hydrocarbon solvents such as pentane, hexane, heptane, octane, nonane, decane, and isododecane, alcoholic solvents such as ethanol, propanol, butanol, isopropanol, and isobutanol, or benzene, toluene, or xylene. Aromatic solvents such as 1 wt% to 10000 wt% based on the aliphatic ketone (that is, 1 wt% aliphatic ketone based on the total weight of the solvent) can be used. As the solvent, heptane, octane, nonane, decane, isododecane, ethanol, propanol, toluene, or xylene is preferable from the viewpoint of industrial handling and availability, and octane, isododecane, ethanol, or xylene is more preferable. From the industrial viewpoint, it is most preferable to be solvent-free.

The unsaturated bond formed by the intramolecular dehydration reaction by the reduction reaction of the unsaturated bond to the saturated bond, the unsaturated bond originally possessed by the fatty acid used as the raw material, and the unsaturated bond formed by the previous reaction. Saturated bonds are also reduced. For this reason, by sufficiently carrying out the reduction reaction, the content of unsaturated hydrocarbons is extremely small or consists only of saturated hydrocarbons (that is, the content of unsaturated hydrocarbons in a normal detection method). A composition (below the detection limit) is obtained.

[Wax-like composition]
The composition obtained by the method for producing a waxy composition of the present invention is in the form of a wax (solid at 25 ° C.) containing saturated hydrocarbon as a main component. In particular, the wax composition has a very low content of high-molecular-weight or high-melting concomitant compounds and impurities whose structure is unknown, compared to conventional paraffin wax produced from crude oil. Excellent releasability, water repellency, waterproofness and anti-blocking property.

That is, in the composition obtained by the method for producing a waxy composition of the present invention, the fatty acid residue constituting the fatty acid composition or the metal soap is (1) the linear fatty acid content is based on the total mass of the total fatty acids. 30% by mass or more and 100% by mass or less, or (2) the content of linear fatty acids is 25% by mass or more and less than 30% by mass with respect to the total mass of total fatty acids, and 2 or 3 carboxylic acids A composition containing an aliphatic ketone obtained after decarboxylating dimerization reaction is performed on a fatty acid composition containing no branched-chain fatty acids that are liquid at 25 ° C. or having a content below the detection limit a hydrocarbon composition obtained by carrying out the hydrodeoxygenation reaction against the molar abundance ^{ratio, 14 C,} isotopes to moles existence ratio of ^{12 C} isotope in carbon atoms constituting the hydrocarbon composition Ratio of a waxy composition containing carbon in the range of ^{6 × 10 -13 ~ 1.2 × 10} -12.
The 180 ° peel stress range of the wax-like composition is preferably 180 g or less, more preferably 160 g or less, and even more preferably 155 g or less. The peeling stress is measured under the measurement conditions described later.
The initial contact angle range of the wax-like composition is preferably 95 ° or more, more preferably 115 ° or more, and even more preferably 118 ° or more. Moreover, the range of the contact angle after the wax-like composition is immersed in distilled water is preferably 80 ° or more, more preferably 100 ° or more, further preferably 104 ° or more, and the larger the value. Further, the difference in contact angle before and after immersion in distilled water is preferably 20 ° or less, more preferably 18 ° or less, further preferably 15 ° or less, and the smaller the better. The initial contact angle and the contact angle after immersion in distilled water are measured under the measurement conditions described below.

The wax-like composition can be suitably used as a raw material for various products, particularly as a substitute for paraffin wax. For example, the wax-like composition can be suitably used as a releasability improver, moldability improver, polish, waterproofing or water repellency imparting agent.

Also, the waxy composition can be used as it is as a raw material for cosmetics, pharmaceuticals, or quasi drugs. When the wax-like composition is used as a kind of raw material for cosmetics and the like, the content of the wax-like composition in the cosmetics and the like is 0. 0% with respect to the total mass of all the components constituting the cosmetics and the like. It can be 1 to 95% by mass, preferably 0.5 to 90% by mass, and more preferably 1 to 80% by mass.

When the wax-like composition of the present invention is used as a mold release improver, the composition of the present invention is heated, melted, emulsified, or solubilized together with any additive generally added to the mold release improver. Can be used. Additives here are, for example, detergent dispersants, antioxidants, oiliness improvers, antiwear agents, extreme pressure additives, rust inhibitors, corrosion inhibitors, metal deactivators, viscosity index improvers, pour points. Depressants, antifoaming agents, emulsifiers, demulsifiers, antifungal preservatives and the like can be mentioned. As the form of the lubricity improver, oil dissolution type; emulsification type such as O / W type, W / O type, W / O / W type, or O / W / O type; solubilization type; or solid type Can take any desired form.
Examples of the mold release improver include divider oil, concrete mold release oil, cast mold release oil, rubber mold release oil, and plastic mold release oil.
When the waxy composition of the present invention is used as a moldability improver, the composition of the present invention is heated, melted, emulsified, or solubilized together with any additive generally added to the moldability improver. Can be used. Additives here are, for example, crystal modifiers, oil agents, detergent dispersants, antioxidants, oiliness improvers, anti-friction agents, abrasives, rust inhibitors, corrosion inhibitors, UV absorbers, UV scattering agents, Metal deactivator, viscosity index improver, antifoaming agent, emulsifier, demulsifier, antifungal preservative, hydrocarbon wax, ester wax, petroleum resin, terpene resin, petroleum oil agent, ester oil agent, polymer system Examples thereof include a resin or a solvent. As a form of a moldability improvement agent, desired forms, such as an oil melt | dissolution type or a solid type, can be taken. Formability improvers improve the formability of a product group whose final form is solid. For example, the moldability improver for solid cosmetics, the moldability improvement for solid pharmaceuticals and quasi drugs And moldability improvers such as agents and candles.
When the waxy composition of the present invention is used as a polishing agent, the composition of the present invention is used by melting, emulsifying, or solubilizing the composition of the present invention together with any additive generally added to the polishing agent. be able to. Additives here are, for example, detergent dispersants, antioxidants, oiliness improvers, anti-friction agents, abrasives, rust inhibitors, corrosion inhibitors, UV absorbers, UV scattering agents, metal deactivators, viscosity Index improver, antifoaming agent, emulsifier, demulsifier, antifungal preservative, hydrocarbon wax, ester wax, petroleum resin, terpene resin, petroleum oil agent, ester oil agent, polymer resin, solvent, or water Etc. As the form of the polishing agent, an oil dissolution type; an emulsification type such as O / W type, W / O type, W / O / W type, or O / W / O type; a solubilization type; or a solid type It can take any desired form. The above-mentioned polishing agents include: polishing agents for automobiles, polishing agents for metal materials, flooring agents, lustering agents for wood, polishing agents for plastics, polishing agents for ceramics, polishing agents for rubber, leather And a polishing agent for cloth or a polishing agent for cloth.
When the wax-like composition of the present invention is used as a waterproof or water-repellent imparting agent, the composition of the present invention is melted or emulsified or emulsified with an optional additive generally incorporated into a polish. It can be used after solubilization. Additives here are, for example, detergent dispersants, antioxidants, oiliness improvers, anti-friction agents, abrasives, rust inhibitors, corrosion inhibitors, UV absorbers, UV scattering agents, metal deactivators, viscosity Index improver, antifoaming agent, emulsifier, demulsifier, antifungal preservative, hydrocarbon wax, ester wax, petroleum resin, terpene resin, petroleum oil agent, ester oil agent, polymer resin, solvent, or water Etc. As the form of the polishing agent, an oil dissolution type; an emulsification type such as O / W type, W / O type, W / O / W type, or O / W / O type; a solubilization type; or a solid type It can take any desired form. The waterproof or water-repellent imparting agent is a water repellent for automobiles, a water repellent for metal materials, a floor water repellent, a wood water repellent, a plastic water repellent, a ceramic water repellent, and a rubber. Water repellent, leather water repellent, cloth water repellent, and the like.

The form of the cosmetic containing the wax-like composition is not particularly limited, but is preferably a solid cosmetic. Examples of the solid cosmetic include lipstick, lip balm, lip gloss, powder foundation, stick concealer, eye color pencil, clay wax, and hair wax.

The cosmetics, pharmaceuticals, or quasi-drugs containing the wax-like composition may be blended with various components generally used in cosmetics, etc., if desired, and manufactured by a conventionally known method. For example, anionic surfactant, cationic surfactant, amphoteric surfactant, lipophilic nonionic surfactant, hydrophilic nonionic surfactant, silicone surfactant, natural surfactant, liquid fat, solid fat Waxes, hydrocarbon oils, higher fatty acids, higher alcohols, ester oils, silicone oils, powders, humectants, natural water-soluble polymers, semi-synthetic water-soluble polymers, synthetic water-soluble polymers, inorganic Water-soluble polymer, thickener, ultraviolet absorber, sequestering agent, lower alcohol, polyhydric alcohol, monosaccharide, oligosaccharide, polysaccharide, amino acid, organic amine, synthetic resin emulsion, pH adjuster, vitamins, oxidation An inhibitor, an antioxidant assistant, a fragrance, water, and the like can be appropriately blended as desired.

The method for producing a waxy composition according to still another aspect of the present invention includes:
Fatty acid composition
(1) The content of linear fatty acids is 30% by mass or more and 100% by mass or less with respect to the total mass of total fatty acids, or (2) the content of linear fatty acids is 25% by mass with respect to the total mass of total fatty acids. % Is less than 30% by mass and does not contain a branched chain fatty acid that is liquid at 25 ° C. having 2 or 3 carboxylic acids, or the content is below the detection limit,
A method for producing a waxy composition comprising performing a decarboxylation dimerization reaction on a fatty acid composition and then performing a hydrodeoxygenation reaction on the resulting composition containing an aliphatic ketone. There,
The linear fatty acid includes linear fatty acid having one carboxylic acid having 10 to 22 carbon atoms and sebacic acid,
The content of the sebacic acid with respect to the total mass of the total fatty acids is ½ or less of the content with respect to the total mass of the total fatty acids of the linear fatty acids,
The branched fatty acid in liquid form at 25 ° C. having 2 or 3 carboxylic acids is a branched chain fatty acid having 36 carbon atoms having 2 carboxylic acids and a branched chain fatty acid having 54 carbon atoms having 3 carboxylic acids. At least one fatty acid selected from the group consisting of:
The fatty acid composition further comprises isostearic acid,
The decarboxylation dimerization reaction is performed in the presence of at least one metal selected from the group consisting of magnesium oxide, magnesium hydroxide, calcium oxide, calcium hydroxide, zinc oxide, and zinc hydroxide;
The hydrodeoxygenation reaction is a reaction in which a ketone group is reduced to a methylene group, and is performed in the presence of hydrazine or zinc amalgam,
The hydrodeoxygenation reaction involves reducing the aliphatic ketone to synthesize an aliphatic alcohol, and reducing the ketone to form an unsaturated bond by intramolecular dehydration of the resulting aliphatic alcohol. A reaction and a reduction reaction of the unsaturated bond to obtain a saturated hydrocarbon by reducing the hydrocarbon in which the unsaturated bond is formed by the intramolecular dehydration reaction,
At least one of the reduction reaction of the ketone and the reduction reaction of the unsaturated bond is at least one selected from the group consisting of Pt, Pd, Ni, Cu, Cr, Ru, Rh, Li, Al, B, and Zn. A reaction performed in the presence of a metal, and
The intramolecular dehydration reaction is a reaction performed in the presence of at least one of a Bronsted acid and a Bronsted base;
The ratio of the mole fraction of ¹⁴ C isotope to the mole fraction of ¹² C isotope in the fatty acid composition is preferably in the range of 6 × 10 ⁻¹³ to 1.2 × 10 ⁻¹² .

The method for producing a waxy composition according to still another aspect of the present invention includes:
Fatty acid composition
(1) The content of linear fatty acids is 30% by mass or more and 100% by mass or less with respect to the total mass of total fatty acids, or (2) the content of linear fatty acids is 25% by mass with respect to the total mass of total fatty acids. % Is less than 30% by mass and does not contain a branched chain fatty acid that is liquid at 25 ° C. having 2 or 3 carboxylic acids, or the content is below the detection limit,
Decarboxylation reaction on metal soap synthesized by fatty acid composition and at least one compound selected from the group consisting of magnesium oxide, magnesium hydroxide, calcium oxide, calcium hydroxide, zinc oxide, and zinc hydroxide A method for producing a wax-like composition comprising performing a hydrodeoxygenation reaction on the resulting composition containing an aliphatic ketone after
The linear fatty acid is a linear fatty acid having one carboxylic acid having 10 to 22 carbon atoms and sebacic acid,
The branched fatty acid in liquid form at 25 ° C. having 2 or 3 carboxylic acids is a branched chain fatty acid having 36 carbon atoms having 2 carboxylic acids and a branched chain fatty acid having 54 carbon atoms having 3 carboxylic acids. At least one fatty acid selected from the group consisting of:
The fatty acid composition further comprises isostearic acid,
The hydrodeoxygenation reaction is a reaction in which a ketone group is reduced to a methylene group, and is performed in the presence of hydrazine or zinc amalgam,
The hydrodeoxygenation reaction involves reducing the aliphatic ketone to synthesize an aliphatic alcohol, and reducing the ketone to form an unsaturated bond by intramolecular dehydration of the resulting aliphatic alcohol. A reaction and a reduction reaction of the unsaturated bond to obtain a saturated hydrocarbon by reducing the hydrocarbon in which the unsaturated bond is formed by the intramolecular dehydration reaction,
At least one of the reduction reaction of the ketone and the reduction reaction of the unsaturated bond is at least one selected from the group consisting of Pt, Pd, Ni, Cu, Cr, Ru, Rh, Li, Al, B, and Zn. A reaction performed in the presence of a metal, and
The intramolecular dehydration reaction is a reaction performed in the presence of at least one of a Bronsted acid and a Bronsted base;
The ratio of the mole fraction of ¹⁴ C isotope to the mole fraction of ¹² C isotope in the fatty acid composition is preferably in the range of 6 × 10 ⁻¹³ to 1.2 × 10 ⁻¹² .

The fatty acid in the fatty acid composition is preferably derived from a plant or an animal, more preferably from a plant due to industrial availability, soybean, palm, palm kernel, rapeseed, sunflower, cottonseed More preferred are peanut, peanut, corn, olive, sesame, flaxseed, castor or pine.

The method for producing a waxy composition according to still another aspect of the present invention includes:
Fatty acid composition
(1) The content of linear fatty acids is 30% by mass or more and 100% by mass or less with respect to the total mass of total fatty acids, or (2) the content of linear fatty acids is 25% by mass with respect to the total mass of total fatty acids. % Is less than 30% by mass and does not contain a branched chain fatty acid that is liquid at 25 ° C. having 2 or 3 carboxylic acids, or the content is below the detection limit,
Decarboxylation reaction on metal soap synthesized by fatty acid composition and at least one compound selected from the group consisting of magnesium oxide, magnesium hydroxide, calcium oxide, calcium hydroxide, zinc oxide, and zinc hydroxide A method for producing a wax-like composition comprising performing a hydrodeoxygenation reaction on the resulting composition containing an aliphatic ketone after
The linear fatty acid comprises at least one linear fatty acid selected from the group consisting of capric acid, lauric acid, myristic acid, palmitic acid, stearic acid, arachidic acid, behenic acid, and sebacic acid,
The branched fatty acid in liquid form at 25 ° C. having 2 or 3 carboxylic acids is a branched chain fatty acid having 36 carbon atoms having 2 carboxylic acids and a branched chain fatty acid having 54 carbon atoms having 3 carboxylic acids. Comprising at least one fatty acid selected from the group consisting of
The fatty acid composition further comprises isostearic acid,
The hydrodeoxygenation reaction is a reaction in which a ketone group is reduced to a methylene group, and is performed in the presence of hydrazine or zinc amalgam,
The hydrodeoxygenation reaction involves reducing the aliphatic ketone to synthesize an aliphatic alcohol, and reducing the ketone to form an unsaturated bond by intramolecular dehydration of the resulting aliphatic alcohol. A reaction and a reduction reaction of the unsaturated bond to obtain a saturated hydrocarbon by reducing the hydrocarbon in which the unsaturated bond is formed by the intramolecular dehydration reaction,
At least one of the reduction reaction of the ketone and the reduction reaction of the unsaturated bond is at least one selected from the group consisting of Pt, Pd, Ni, Cu, Cr, Ru, Rh, Li, Al, B, and Zn. A reaction performed in the presence of a metal, and
The intramolecular dehydration reaction is a reaction performed in the presence of at least one of a Bronsted acid and a Bronsted base;
The ratio of the mole fraction of ¹⁴ C isotope to the mole fraction of ¹² C isotope in the fatty acid composition is preferably in the range of 6 × 10 ⁻¹³ to 1.2 × 10 ⁻¹² .

Hereinafter, the present invention will be described in more detail based on specific examples. The present invention is not limited to the contents of the examples shown below.

[Example 1; Synthesis of waxy hydrocarbon composition]
A 2 L four-necked flask equipped with a stirrer, a thermometer, a nitrogen gas inlet tube and a water separator was charged with 591 g of pharmacopoeia magnesium stearate [product name: JPM-100 (manufactured by Sakai Chemical Co., Ltd.)] at 320 ° C. The reaction was performed for 12 hours. The progress of the reaction was confirmed by extracting a part of the reaction mixture, neutralizing with 2N hydrochloric acid (manufactured by Wako Pure Chemical Industries), dissolving in xylene, and confirming that the peak of stearic acid disappeared by gas chromatography. Next, 5 wt% of Pd / C (manufactured by Sigma-Aldrich) is charged into the pressure-resistant metal container with respect to the total amount of raw material fatty acids (the amount of pharmacopoeia magnesium stearate), and after removing the headspace air under reduced pressure, hydrogen The gas was continuously introduced at a pressure of 1 MPa and reacted at 240 ° C. for 6 hours. Once Pd / C and the released magnesium oxide powder were removed by filtration, 5 wt% of activated clay was added to the amount of pharmacopeia magnesium stearate, and the reaction was carried out at 200 ° C. for 6 hours under normal pressure. Further, after the activated clay was removed by filtration, 2 wt% of nickel oxide was charged, hydrogen gas was continuously introduced at a pressure of 0.5 MPa, and reacted at 150 ° C. for 6 hours. Nickel oxide was removed by filtration to obtain 312 g of a solid hydrocarbon composition. The purity of the obtained solid hydrocarbon composition was confirmed by gas chromatography [GC-2010 column; DB-5HT detector; FID (manufactured by Shimadzu Corporation)].

[Example 2; Synthesis of waxy hydrocarbon composition]
In a 2 L four-necked flask equipped with a stirrer, a thermometer, a nitrogen gas inlet tube and a water separator, myristic acid [product name: PALMAC98-14 (manufactured by ACIDCHEM)] 133.6 g, palmitic acid [product name: PALMAC98] -16 (manufactured by ACIDCHEM)] 300.0 g, stearic acid [product name: PALMAC98-18 (manufactured by ACIDCHEM)] 166.4 g, zinc oxide (manufactured by Wako Pure Chemical Industries) 95.4 g, magnesium oxide [product name: 4.7 g of industrial magnesium oxide (manufactured by Kyowa Chemical Industry Co., Ltd.)] was charged and reacted at 280 ° C. for 10 hours. The progress of the reaction was confirmed by extracting a part of the reaction mixture and neutralizing it with 2N hydrochloric acid (manufactured by Wako Pure Chemical Industries, Ltd.) and dissolving it in xylene and confirming that the fatty acid peak disappeared by gas chromatography. After the generated zinc oxide and magnesium oxide were removed by filtration, 408 g of a white solid aliphatic ketone mixture was obtained. This white solid was dissolved in anhydrous diethyl ether, and 38 g of lithium aluminum hydride (manufactured by Kanto Chemical Co., Inc.) was added and reacted for 1 hour under an argon atmosphere. After confirming disappearance of the peak of the ketone compound by gas chromatography, a saturated aqueous solution of potassium sodium tartrate was gradually added, followed by stirring for 1 hour. After the aqueous layer was separated, the solvent was distilled off under reduced pressure to obtain 405 g of a white solid alcohol composition. The alcohol composition was charged with 5 wt% activated clay and 2 wt% nickel oxide, and hydrogen gas was continuously introduced at a pressure of 1 MPa and reacted at 150 ° C. for 6 hours. The activated clay and nickel oxide were removed by filtration to obtain 312 g of a solid hydrocarbon composition. The purity of the obtained solid hydrocarbon composition was confirmed by gas chromatography [GC-2010 column; DB-5HT detector; FID (manufactured by Shimadzu Corporation)].

[Example 3; Synthesis of waxy hydrocarbon composition]
In a 2 L four-necked flask equipped with a stirrer, a thermometer, a nitrogen gas inlet tube and a water separator, myristic acid [product name: PALMAC 98-14 (manufactured by ACIDCHEM)] 133.6 g, calcium palmitate [product name: ZS-16 (manufactured by Nitto Kasei Kogyo Co., Ltd.)] 644.6 g, zinc stearate [product name: zinc stearate (manufactured by Wako Pure Chemical Industries)] 369.9 g, magnesium oxide [product name: industrial magnesium oxide (Kyowa Chemical) (Made by Kogyo Co., Ltd.)] 23.6 g was charged and reacted at 280 ° C. for 10 hours. The progress of the reaction was confirmed by extracting a part of the reaction mixture and neutralizing it with 2N hydrochloric acid (manufactured by Wako Pure Chemical Industries, Ltd.) and dissolving it in xylene and confirming that the fatty acid peak disappeared by gas chromatography. After removing the produced powder by filtration, 385 g of a light yellow solid aliphatic ketone mixture was obtained. A pale yellow solid was charged into a 1 L pressure-resistant metal container together with 3.8 g of diatomite-supported composite type stable oxidized Ni / Cu / Cr [product name: N113B (manufactured by JGC Catalysts & Chemicals)], and the air in the headspace was reduced under reduced pressure. Then, hydrogen gas was continuously introduced at a pressure of 1 MPa and reacted at 200 ° C. for 10 hours. Then, 3.8 g of activated clay was added and reacted at 200 ° C. under normal pressure for 6 hours. Furthermore, after removing the air in the head space again under reduced pressure, hydrogen gas was continuously introduced at a pressure of 0.7 MPa and reacted at 180 ° C. for 10 hours. Diatomite-supported stable oxidized Ni / oxidized Cu / oxidized Cr and activated clay were removed by filtration to obtain 282 g of a white solid hydrocarbon composition. The composition of the obtained hydrocarbon composition was confirmed by gas chromatography [GC-2010 column; DB-5HT, detector; FID (manufactured by Shimadzu Corporation)], and the composition was the same as in Example 2. confirmed.

The hydrocarbon composition obtained in Example 2 was evaluated for thermal properties, moldability, stability (perspiration), releasability, water repellency and waterproofness, and antiblocking properties. As Comparative Example 1, a commercially available paraffin wax [product name: 155F (manufactured by Nippon Seiwa)] was used.

<Measurement of thermal properties by differential scanning calorimetry>
The thermal properties of each hydrocarbon composition were measured with a differential scanning calorimeter (DSC).
The measurement results are shown in Table 1. The difference between the melting start temperature and the melting end temperature of the hydrocarbon composition of Example 2 was smaller than that of the hydrocarbon composition of Comparative Example 1. This suggested that the content of low-boiling contaminants is low.

<Formability evaluation and stability evaluation>
(Sample preparation for moldability evaluation and stability evaluation test)
The components shown in Table 2 were weighed and dissolved on a plate heater heated to 100 ° C. while stirring with a glass rod. The dissolved mixture was dispensed onto five 20 mm square, 5 mm deep stainless steel trays heated on a 100 ° C. plate heater. Two of the five pieces were transferred to an aluminum plate that was allowed to stand at room temperature of 25 ° C., and rapidly cooled and solidified to room temperature, which was used as a quenched sample. Of the remaining 3 sheets, 2 sheets were stopped from heating by the plate heater and cooled to room temperature over 1 hour as slow-cooled samples. The remaining one sheet was left in a constant temperature bath at 25 ° C. to prepare a comparative sample for the stability evaluation test.

(Evaluation of formability)
The surface state of the sample prepared above was visually confirmed.
A: There is no unevenness and the surface is smooth.
B: There are some irregularities and the surface is slightly rough.
C: Remarkable irregularities exist and the surface is rough.

(Evaluation of stability (perspiration))
The four samples prepared above were allowed to stand for 48 hours in a thermostatic chamber in which the chamber temperatures were 20 ° C. and 40 ° C. for one cycle in 24 hours, and the sample was removed from the chamber when the chamber temperature was 40 ° C. I took it out. The changes in the surface state immediately after removal and the change in the surface state after standing at room temperature of 25 ° C. for 1 hour were visually compared with the reference sample for each sample.

Evaluation criteria for surface condition immediately after removal;
A: There is no change in the surface state compared with the standard product.
B: Slight drop-like sweating is observed on the surface as compared with the standard product.
C: Drop-like sweating is noticeably observed on the surface as compared with the standard product.
Evaluation criteria for changes in surface condition after standing at 25 ° C. for 1 hour;
A: There is no change in the surface state compared with the standard product.
B: The surface unevenness is slightly increased as compared with the standard product.
C: The unevenness | corrugation of the surface is increasing notably compared with a sample.

Table 3 shows the evaluation results of moldability and the evaluation results of stability (perspiration). As a result, the hydrocarbon composition of Example 2 had better moldability and better stability (perspiration) than the hydrocarbon composition of Comparative Example 1.

<Evaluation of releasability, water repellency, waterproofness and antiblocking>
As the evaluation of releasability, water repellency and waterproofing, and anti-blocking property, the tape peelability and anti-blocking property of the wax-impregnated paper were evaluated.

(Preparation of wax-impregnated paper for evaluation)
The wax-impregnated paper is impregnated by a dip coating method in which a commercially available A5 size PPC copy paper (weight per sheet: 2.05 g) is immersed in a wax solution obtained by dissolving each hydrocarbon composition at 100 ° C. After the wax solidified, excess wax was removed with a stainless scraper.

(Evaluation of releasability)
1A to 1C schematically show the evaluation method. A test piece 1 of 5 cm × 4 cm is prepared from the wax-impregnated paper prepared above, and a 2 cm × 6 cm vinyl tape 2 is attached to the center of the test piece 1 (FIG. 1A), and a compression molding machine [model name: AYSR- 5 (manufactured by Shinfuji Metal Industry Co., Ltd.)] for 30 minutes at a pressure of 1 MPa. After 30 minutes, the other part of the vinyl tape 2 was peeled off, leaving a 2 cm × 2 cm part (FIG. 1B). Next, the peeled portion of the vinyl tape 2 and the portion of the test piece 1 where the vinyl tape 2 is not adhered are sandwiched between a pair of adapters (3a, 3b) of the FUDOH rheometer (FIG. 1C), and 180 ° peel stress Was measured under the following conditions. Measurement was carried out with four test pieces for each hydrocarbon composition, and the average value of the maximum stress of the measurement was calculated.
Measurement condition;
Measuring instrument: FUDOH rheometer (manufactured by Rheotech)
Adapter: Tensile universal adapter Sample table lowering speed: 6 cm / min Down stroke: 2 cm

(Evaluation of water repellency)
For water repellency, the contact angle of water droplets formed when 100 μL of distilled water (manufactured by Wako Pure Chemical Industries, Ltd.) was dropped on the prepared wax-impregnated paper was calculated by the tangential method, and was used as the initial contact angle. Further, the waterproof property was measured by immersing the test piece whose water repellency was measured in distilled water at 45 ° C. for 1 hour and then measuring the contact angle between the test piece and the water droplet again.

(Evaluation of anti-blocking properties)
Five sheets of the prepared wax-impregnated paper were stacked and allowed to stand for 3 days at a constant temperature of 50 ° C. with a weight of 150 g from the top. After 3 days, the weight was removed, and the state (anti-blocking property) when the five impregnated papers were peeled off was evaluated.
Evaluation criteria for anti-blocking properties;
A: Blocking is not recognized, and the five impregnated papers can be easily peeled off.
B: Although slight blocking is recognized, 5 sheets of impregnated paper can be peeled.
C: There is impregnated paper in which remarkable blocking is recognized and it cannot be peeled out of 5 sheets.

Table 4 shows the average value of the maximum stress, the initial contact angle of water droplets, the measurement result of contact angle after immersion in distilled water, the difference in contact angle before and after immersion, and the anti-blocking evaluation result. As a result, it was found that the hydrocarbon compositions of Examples 1 and 2 had lower stress and excellent mold release properties than the hydrocarbon composition of Comparative Example 1. In addition, the initial contact angle is almost the same, but the contact angle after immersion in distilled water is larger for the hydrocarbon compositions of Examples 1 and 2 than for the hydrocarbon composition of Comparative Example 1. It was also confirmed that the hydrocarbon compositions of No. 1 and No. 2 were excellent in water repellency. Further, the hydrocarbon compositions of Examples 1 and 2 also had good antiblocking properties.

[Examples 3 to 9, Comparative Examples 1 to 7]
A hydrocarbon composition was obtained in the same manner as in Example 2 except that the raw fatty acid composition was changed to the fatty acid composition shown in Tables 5 and 6. In Tables 5 and 6, “C10” is capric acid [product name: PALMAC 99-10 (manufactured by ACIDCHEM)], “C12” is lauric acid [product name: PALMAC98-12 (manufactured by ACIDCHEM)], “C14”. Is myristic acid [product name: PALMAC98-14 (manufactured by ACIDCHEM)] “C16” is palmitic acid [product name: PALMAC98-16 (manufactured by ACIDCHEM)], “C18” is stearic acid [product name: PALMAC98-18 ( ACIDCHEM)], “C20” is arachidic acid, “C22” is behenic acid (a mixture of arachidic acid / behenic acid [product name: EDENOR C20-22 (manufactured by Cognis)]), “SLMFA” is 1 carvone The total mass of linear fatty acids having acid, “C10DA” is sebacic acid [product name: sebacic acid ( Kuroda Gosei Kogyo Co., Ltd.)], “Dimer” is purified dimer acid [Product name: EMPOL 1012 (Cognis)], “iC18” is isostearic acid [Product name: PRISOLINE 3505 (Croda)], “iFA” is The total mass of branched chain fatty acids is shown. “Dimer / iFA” indicates the content of the purified dimer acid relative to the total mass of the branched chain fatty acid.
The numerical values shown in the raw material fatty acid compositions in Tables 5 and 6 are values obtained by rounding off the second decimal place.

Regarding the releasability measurement in Comparative Examples 2 to 8, since the shape was paste, the wax did not solidify after the wax impregnation, and it was difficult to prepare a wax-impregnated paper suitable for the measurement (Table 6). "N.D.").

The purified dimer acid and isostearic acid used were analyzed by GPC (Gel Permeation Chromatography), and no peak was detected on the left side of the dimer acid in the chromatograph. That is, it was confirmed that the purified dimer acid and isostearic acid used did not contain trimer acid at a level detectable by GPC.

As a result, the hydrocarbon compositions of Examples 1 to 9 in which the linear fatty acid content (total content of SLMFA and C10DA) in the raw fatty acid composition was 25% by mass or more based on the total mass of the total fatty acids were It was waxy.
On the other hand, the hydrocarbon compositions of Comparative Examples 2 to 4 whose linear fatty acid content was less than 25% by mass with respect to the total mass of the total fatty acids were liquid or pasty. The hydrocarbon compositions of Comparative Examples 5 to 8 having a linear fatty acid content of 25% by mass or more and less than 30% by mass with respect to the total mass of the total fatty acids and containing dimer acid were paste-like. there were.

The wax-like composition obtained by the method for producing a wax-like composition of the present invention is excellent in moldability, stability, releasability, water repellency, waterproofness, and anti-blocking property, and as a paraffin wax substitute Since it is suitable, it is useful as an industrial base material in various industrial products such as cosmetics, ointment bases in pharmaceuticals, industrial lubricants and mold release agents.

1 ... Test piece (wax impregnated paper), W ... Wax, 2 ... Vinyl tape, 3a, 3b ... Rheometer adapter.

Claims (30)

Fatty acid composition
(1) The content of linear fatty acids is 30% by mass or more and 100% by mass or less with respect to the total mass of total fatty acids, or (2) the content of linear fatty acids is 25% by mass with respect to the total mass of total fatty acids. % Is less than 30% by mass and does not contain a branched chain fatty acid that is liquid at 25 ° C. having 2 or 3 carboxylic acids, or the content is below the detection limit,
A method for producing a wax-like composition, comprising performing a decarboxylation dimerization reaction on a fatty acid composition and then performing a hydrodeoxygenation reaction on the resulting composition containing an aliphatic ketone. The branched fatty acid in liquid form at 25 ° C. having 2 or 3 carboxylic acids is a branched chain fatty acid having 36 carbon atoms having 2 carboxylic acids and a branched chain fatty acid having 54 carbon atoms having 3 carboxylic acids. The method for producing a waxy composition according to claim 1, which is at least one fatty acid selected from the group consisting of: The linear fatty acid comprises at least one linear fatty acid selected from the group consisting of a linear fatty acid having one carboxylic acid and a linear fatty acid having two carboxylic acids;
The content of the linear fatty acid having the two carboxylic acids with respect to the total mass of the total fatty acids is ½ or less of the content with respect to the total mass of the total fatty acids of the linear fatty acids. A process for producing the described waxy composition. The wax-like composition according to any one of claims 1 to 3, wherein the linear fatty acid having two carboxylic acids is a linear fatty acid having 4 to 10 carbon atoms having two carboxylic acids. Production method. The method for producing a wax-like composition according to any one of claims 1 to 3, wherein the linear fatty acid having one carboxylic acid in the fatty acid composition is a linear fatty acid having 10 to 22 carbon atoms. . The decarboxylation dimerization reaction is performed in the presence of at least one metal atom selected from the group consisting of Group II and Group VII to XII metal atoms. A process for producing the described waxy composition. The decarboxylation dimerization reaction is performed in the presence of at least one metal selected from the group consisting of Mg, Ca, Mn, Fe, Co, Ni, Cu, and Zn. A method for producing the wax-like composition according to claim 1. The method for producing a wax-like composition according to claim 7, wherein the metal is an oxide or a hydroxide. Fatty acid composition
(1) The content of linear fatty acids is 30% by mass or more and 100% by mass or less with respect to the total mass of total fatty acids, or (2) the content of linear fatty acids is 25% by mass with respect to the total mass of total fatty acids. % Is less than 30% by mass and does not contain a branched chain fatty acid that is liquid at 25 ° C. having 2 or 3 carboxylic acids, or the content is below the detection limit,
Fat obtained by performing decarboxylation on a metal soap synthesized with a fatty acid composition and at least one metal atom selected from the group consisting of Group II and Group VII to XII metal atoms The manufacturing method of a wax-like composition including performing hydrodeoxygenation reaction with respect to the composition containing a group ketone. The method for producing a wax-like composition according to claim 9, wherein the metal soap is composed of an alkaline earth metal bonded to two linear fatty acid residues. The wax-like composition according to claim 9, wherein the metal soap is a metal soap containing at least one metal selected from the group consisting of Mg, Ca, Mn, Fe, Co, Ni, Cu, and Zn. Production method. The wax-like composition according to any one of claims 1 to 11, wherein the hydrodeoxygenation reaction is a reaction in which a ketone group is reduced to a methylene group, and is performed in the presence of hydrazine or zinc amalgam. Manufacturing method. The hydrodeoxygenation reaction is
A reduction reaction of the ketone for reducing the aliphatic ketone and synthesizing the aliphatic alcohol;
Intramolecular dehydration reaction in which the obtained aliphatic alcohol is dehydrated intramolecularly to form an unsaturated bond;
A reduction reaction of the unsaturated bond to obtain a saturated hydrocarbon by reducing the hydrocarbon in which the unsaturated bond is formed by the intramolecular dehydration reaction;
The method for producing a wax-like composition according to any one of claims 1 to 11, comprising: At least one of the reduction reaction of the ketone and the reduction reaction of the unsaturated bond is at least one selected from the group consisting of Pt, Pd, Ni, Cu, Cr, Ru, Rh, Li, Al, B, and Zn. The manufacturing method of the wax-like composition of Claim 13 performed in presence of a metal. The method for producing a wax-like composition according to claim 13, wherein the intramolecular dehydration reaction is performed in the presence of at least one of a Bronsted acid and a Bronsted base. The ratio of the molar abundance ratio of ¹⁴ C isotope to the molar abundance ratio of ¹² C isotope in the fatty acid composition is in the range of 6 × 10 ⁻¹³ to 1.2 × 10 ⁻¹² . The manufacturing method of the wax-like composition as described in any one. The wax-like composition production method according to any one of claims 1 to 16, wherein the ratio of the molar abundance ratio of ¹⁴ C isotope to the molar abundance ratio of ¹² C isotope is 6 × 10 ^−13. A waxy composition in the range of ^˜1.2 × 10 ⁻¹² . The wax-like composition according to claim 17, which is used as an alternative to paraffin wax. The wax-like composition of Claim 17 used as a mold release improvement agent. The wax-like composition according to claim 17, which is used as a moldability improver. The wax-like composition according to claim 17, which is used as a polish. The wax-like composition according to claim 17, which is used as a waterproof or water-repellent imparting agent. The wax-like composition of Claim 17 used for cosmetics. Fatty acid composition
(1) The content of linear fatty acids is 30% by mass or more and 100% by mass or less with respect to the total mass of total fatty acids, or (2) the content of linear fatty acids is 25% by mass with respect to the total mass of total fatty acids. % Is less than 30% by mass and does not contain a branched chain fatty acid that is liquid at 25 ° C. having 2 or 3 carboxylic acids, or the content is below the detection limit,
A waxy composition obtained by subjecting a fatty acid composition to a decarboxylative dimerization reaction and then subjecting the resulting composition containing an aliphatic ketone to a hydrodeoxygenation reaction is A method of using a waxy composition comprising using as a substitute for a wax. Use of the waxy composition according to claim 17 as a substitute for paraffin wax. Use of the waxy composition according to claim 17 as a releasability improver. Use of the waxy composition according to claim 17 as a moldability improver. Use of the wax-like composition according to claim 17 as a polish. Use of the wax-like composition according to claim 17 as a waterproof or water-repellent imparting agent. Use of the waxy composition according to claim 17 as a cosmetic.

Images